Hydrochloric Acid → Mefloquine carboxylic acid

HRID 2286279Notes

Reaction equation

HRID 2286279 reaction equation
[OH-:1].[Na+].[F:3][C:4]([F:17])([F:16])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11](=[O:14])[C:10]2=O.[F:18][C:19]([F:24])([F:23])[C:20]([CH3:22])=O.Cl>O>[F:18][C:19]([F:24])([F:23])[C:20]1[CH:22]=[C:10]([C:11]([OH:1])=[O:14])[C:9]2[C:13](=[C:5]([C:4]([F:17])([F:16])[F:3])[CH:6]=[CH:7][CH:8]=2)[N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9871Methyl trifluoromethyl ketoneHCID 14798Sodium HydroxideHCID 6045757-Trifluoromethylisatin

Product 1

HCID 169721Mefloquine carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 100 parts by volume of water, 8.8 parts of sodium hydroxide, 43.2 parts of 7-trifluoromethyl-isatin and 27.4 parts of 1,1,1-trifluoroacetone is heated for 8 hours at 110° C. in an autoclave. When the mixture has cooled, 2 N hydrochloric acid is added, whilst stirring, until the pH has reached 2.7 and the precipitate formed is filtered off and dried at 70° C. and about 20 mbar. 60 parts of 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid, ie. 97.1% of theory, are obtained.

Workup

  1. temperatureWhen the mixture has cooled
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. customdried at 70° C.
  5. custom97.1% of theory, are obtained

Sources & evidence

ORD record
ord-5a994f325d55415aa1ef95e1c8a42aa6
Source dataset
uspto-grants-1982_04
Patent number
US04327215

Reaction notes

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